Diels-Alder reactions for the rational design of benzo[b]thiophenes: DFT-based guidelines for synthetic chemists

dc.creatorBrasca, Romina
dc.creatorKneeteman, Maria Nelida
dc.creatorMancini, Pedro Maximo Emilio
dc.creatorFabian, Walter M.F.
dc.date2012-02
dc.identifierhttp://hdl.handle.net/11336/96493
dc.identifierBrasca, Romina; Kneeteman, Maria Nelida; Mancini, Pedro Maximo Emilio; Fabian, Walter M.F.; Diels-Alder reactions for the rational design of benzo[b]thiophenes: DFT-based guidelines for synthetic chemists; Elsevier Science; Journal of Molecular Structure; 1010; 2-2012; 158-168
dc.identifier0166-1280
dc.identifierCONICET Digital
dc.identifierCONICET
dc.descriptionIn this work we studied the capability of several diene/dienophile pairs to undergo Diels-Alder (DA) reactions leading to benzo[b]thiophenes. A variety of synthetically and commercially available nitrothiophenes were chosen as dienophiles. Methyl 5-nitro-3-thiophenecarboxylate was selected as a potential strong electrophilic candidate based on some DFT-based properties and the substitution pattern of the expected product. The mechanistic details concerning the participation of this dienophile in polar DA reactions were investigated through a theoretical point of view. The results were compared with the experimental outcomes. This methodology should allow synthetic chemists to analyze DA reactions in detail in a stage prior to the synthetic job.
dc.descriptionFil: Brasca, Romina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional del Litoral; Argentina
dc.descriptionFil: Kneeteman, Maria Nelida. Universidad Nacional del Litoral; Argentina
dc.descriptionFil: Mancini, Pedro Maximo Emilio. Universidad Nacional del Litoral; Argentina
dc.descriptionFil: Fabian, Walter M.F.. Karl-franzens-universitat Graz; Austria
dc.formatapplication/pdf
dc.formatapplication/pdf
dc.languageeng
dc.publisherElsevier Science
dc.relationinfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2011.11.050
dc.rightsinfo:eu-repo/semantics/openAccess
dc.rightshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subjectBENZO[B]THIOPHENES SYNTHESIS
dc.subjectDFT-BASED DESCRIPTORS
dc.subjectNITROTHIOPHENES
dc.subjectPOLAR DIELS-ALDER REACTIONS
dc.subjectREACTION MECHANISM
dc.subjectSUBSTITUTED 1,3-BUTADIENES
dc.subjecthttps://purl.org/becyt/ford/1.4
dc.subjecthttps://purl.org/becyt/ford/1
dc.titleDiels-Alder reactions for the rational design of benzo[b]thiophenes: DFT-based guidelines for synthetic chemists
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:ar-repo/semantics/artículo
dc.typeinfo:eu-repo/semantics/publishedVersion


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